Archive for the ‘Childhood’ Category

This is the story of when I was around 14 years old and my father was trying to get me to grow up a little. I was your typical teenager that went to school and came back and played video games and all that other stuff but my dad didn’t like that much. He wanted me to go out and do things, even if I didn’t have to or even want to.

So, after a few failed ideas, my dad had gotten me a job working for our new neighbour and her name was (lets call her Britney – for confidential issues) and she was incredibly hot. I would sometimes find her sunbathing in her back yard in her bikini and watch her through a small crack in my curtain from my room. She was really hot for a thirty year old, twice my age but at the time, all hot women were the same age to me.

So yeah; my dad said that he had talked to Britney about me doing some house chores for her and so I went with it in hope that it would make him happy. I went over in the morning and knocked on the door and she answered in a quick moment.

“Hello Scott.” Britney said as she opened the door. I couldn’t talk for a moment due to her wearing only a bath robe and nothing else. Unfortunately; it was all tied up at the moment so I couldn’t see her boobs that I would kill to see at 14.

“Hi… Britney.” I said; sounding like an idiot as I tripped over my words and almost failing to look at her eyes and not trying to see if she would have a nipple slip.

“So I’ve been talking with your dad and he says that he wants you to do some chores for me.” Britney said as she guided me into her house. Wasn’t that bad of a house either, very spacious for a woman.

“Yeah; he wants me to grow up a little and stop playing games.” I said; partly I wasn’t complaining because I had gotten to see Britney in her bath robe. I saved that memory for the spank-bank for many years to come.

“Playing games yeah. I love playing games.” Britney said as she guided me to the back yard. Her ass was swaying a little much to be normal. Was she doing it on purpose or is she in a playful mood?

I went with her to the back yard and saw it; it was going to be a long day from the look of it. It was a jungle and I guess it was a job that would take a few hours with the ankle high grass, weeds growing on the fences and a few old trash things that the previous members left behind.

“I want you too clean all this up today and afterwards I’ll have something for you okay.” Britney said as she went back inside and turned on music and danced to it in her bath robe. As for me; I was left out here to cut grass, de-root weeds and pile the old trash into a few garbage bins.

For about 4 hours I was at it until I was finally finished. The grass was cut; weeds de-rooted and the trash in the bins. It looked like a good back yard again. I went inside and went to find Britney.

“Britney; I’m done in the back yard.” I said as I came into the lounge room and found a plate of sandwiches and a nice cup of cold water for me. Britney was just sitting there on the couch in her robe still.

“All done already? Very good, come and sit down with me. Now we have to discuss payment.” Britney said as she patted the spot next to her for me to sit down.

I came to her and sat down. Then suddenly as I sat; Britney straddled me and pinned me to the couch.

“What’s going on?” I asked a little scared and shocked.

“Well; I don’t think you would really want money for all the hard work you did. I saw you out there and I would say that all that work made you have a little tension down stairs. I’m guessing you need a little release.” Britney said as she parted her robe and revealed her boobs to me.

I was so taken back by them that I couldn’t speak even though I wanted to say so much at the time.

“What are you doing?” I asked.

“Pleasing the boy next door.” Britney said as she slid down my body until she was kneeling in front of me. She then took the robe off completely and I was so shocked but now extremely horny that I didn’t move.

“Britney I’m only 14 years old.” I said as she undid my zipper and started taking my pants off along with my boxers.

“I won’t tell if you won’t. I just love underage boys. And plus; would you really say no to me?” Britney asked and I then looked her over again and I could never say no to her. She was a full 10 for me and I had never had anything like this done to me. I’ve seen porn a few times but I would never expect me to be in this type of situation.

“Oh Britney.” I said as my mind shut off and my cock filled with blood so fast that I thought I was about to faint.

“That a boy.” Britney said as she took my pants and boxers to my ankles and grabbed my hard cock in her hands.

“Nice cock for a 14 year old.” Britney said as she started to gently jerk my cock in her hands. I was in heaven already as she stroked me up and down. I had only ever done this to myself but not that she was doing this to me, I was awoken to a new world of pleasure.

“I was just wondering… why you like underage boys?” I asked Britney as she now sped up her strokes.

“Well: I’ve always wanted to be a mommy but I can’t have children and somehow that turned into a taboo fantasy I wanted: To stroke young boys to climax over and over again. I’ve made so many young boys cum now that I don’t even look for people over 18, I’m just a dirty older woman looking for my next school boy to please.” Britney said as she kept on stroking me with her experienced hands.

“How many have you done and how do you do it?” I asked; this story was really getting me off that pre-cum was leaking out of my cock.

“Well; if you promise to keep it a secret, I’ll tell you.” Britney said with her lustful eyes.

“I promise.” I said and that was all I said.

“Well; sometimes I go out and find random boys walking home from school and get them into the car, go to a hidden place and then jerk them off in the back seat. I’ve even gone to the children’s ward of a hospital and milked a few boys there and said it was for the hospital. And now; I’ve got my neighbours kid over at my place and I’m going to make him cum over and over again.” Britney said as she smiled at me and I smiled back at her promise of multiple pleasings.

After about five minutes; I was about to cum and it felt so good.

“You about to cum? I’ve seen that face on many young boys so many times.” Britney said as she sped her strokes up to an incredible speed and cradled my balls with her other hand.

“Oh god; I’m gonna cum.” I said as I felt my cum rise up in my cock and then it happened. I came and I didn’t just cum; I came like a fountain. For a few reasons actually. It has been a few days since I came; Britney was a fantasy I’m living, her stories are hot as fuck and as I came, she squeezed my balls gently and forced more cum to shoot out.

For about 20 seconds; I came in Britney’s hands and she pleasured me into a new world of bliss. My eyes were shut for most of the orgasm so I couldn’t really tel the look on her face but the greatfull moans were good from what I could remember.

After I calmed down from my orgasmic high; Britney looked at me with lust and a sneaky smile.

“You don’t think we’re done here do you?” Britney said.

“What do you mean?” I asked.

“Well; I don’t just please boys once and send them on their way home. I milk them until they can’t walk anymore and I have to drive them home.” Britney said as she used the cum I just came on her hands to lube up her cleavage.

“Wait; your going-” But before I could finish; Britney spoke.

“I’m going to titty fuck you; blow you, fuck you and then maybe even give you my ass before you leave. Young boys can last so much longer than men and have so much more built up tension that I can milk out of them.” Britney said as she squeezed her boobs around my cock and yet again; I was in heaven.

For about three hours; Britney and I were on that couch in total bliss. She did every single thing to me that she said that she was going to do and I loved it. I came a total of five times that day and all due to Britney, my hot as neighbour next door. She was right to; after all that fucking; I couldn’t walk right when I went home, and that was just next door. I lost my virginity to that woman and many other innocent things to her too.

After a great sleep and a big breakfast; I was over the very next day to clean her house. And after that; there was another milking session that went for hours and in different positions.

My dad was proud of me growing up but he never knew that I went over to fuck the next door neighbour multiple times. He honestly thought I was working on her house when really I was cumming five times a day.

For the 2 years it was like this until she moved again and that was a harsh day. She had me addicted to her like a drug and after she left, it was cold turkey and back to me stroking the turkey in memory of her. Funny thing too; I never knew her last name so I couldn’t look her up.

Good thing though; I had run into others that she had fucked over the years and they too were looking for her. A naughty neighbour into underage sex is great. A true taboo fantasy for the ages.

Okay so; when I was about 13 years old I was in that stage of life when I was getting interested in girls and could not keep my hands off of myself. If I saw a hot girl than I was right off to the bathroom to rub one out. Especially when my parents went out and they hired a babysitter to look after me. She was so hot and sexy that I had no control over my penis when she was around. It was just up and down and up and down.

So when my parents went out one night and I was alone with my babysitter Sarah we decided to play hide-n-go-tickle which was really hide n’ seek but one of us gets tickled at the end. So I was hiding once and I was in the closet in my room hiding. I know it seems a little childish playing hide n seek at 13 but it was fun with the huge house we had to play in.

So when I was in the closet with the closet door cracked open a little. I saw Sarah come into the room and she was looking around for me. She looked behind the door and behind the crawl space but she didn’t find me. Then she looked under the bed and then I saw it; her ass was facing my way and the way that the light hit it was very good to see the curves and bubble like structure of her awesome ass. I could feel myself become hard within a matter of seconds by looking at her ass.

Then I accidentally made the floor board below me creak as I was trying to get a better look and she heard it. She came over to the closet in a rush and opened the door and found me. She suddenly tickled me and I collapsed to the ground where she tickled me even further. I had forgotten about the boner I had in my pants until she found it.

“Oh… wow… Sam.” Sarah said as she noticed my boner which for my age was impressive so I was told.

I notices what she was looking at and felt completely embarrassed. I went red with blush and felt completely guilty for looking at her. “I’m sorry; it just happens sometimes.” I said, pathetically.

“It’s okay; it happens to everyone. I should know.” Sarah said as she looked at my boner. I think it was fascination in her eyes as to how big I was.

“Um…” Sarah started.

“What is it?” I asked.

“Do you want me to take care of it for you?” Sarah asked.

“How?” I asked. I had no idea of how she could help me with it but I hoped she could teach me how to control it.

“Just relax and let me take care of it for you.” Sarah said as she grabbed my shorts and boxers and pulled them from my hips and down to my ankles. I couldn’t believe that I was naked in front of Sarah. I felt a little more embarrassed now. I wasn’t sure if I was big enough for a girls liking or if this was even a normal thing.

“Wait, Sarah…” I started but she shushed me with a finger to my mouth.

Suddenly; I was thrown into a world of bliss as she lowered her mouth on to my hard boner and started sucking on my cock. It was so good that I didn’t know how long I would last. I had never had my cock sucked before and I didn’t know that girls did that. I was new to the world of sex and all that stuff but Sarah was my guide now.

I couldn’t believe that my babysitter had her warm wet mouth around my cock and sucking on it like a lollypop. It felt so good. The suction was hard to bear as she went on. Eventually she would come up for breath and then go back to doing what she was doing. She would go all the way down, maybe gag a little and then with incredible suction, come back up and do it all again.

“Does that feel good?” Sarah asked me.

“Yes.” I said. I didn’t know what to say to her but I was over joyed with the pleasure she was giving me.

“Good.” Sarah said before going back to blowing me.

A moment later; I felt something rising up in my balls and cock. It was building fast and hard. I started panting a little faster and getting ready for what was about to come next. I had had about 30 orgasms in my life by this time and none had felt close to what happened next.

“Sarah… I’m…I’m…” I said as I was reaching the point of no return. What ever I did; I couldn’t stop it and I didn’t want to stop it. I didn’t care if I died after this orgasm because it was feeling too good to stop.

“You getting ready to cum?” Sarah said as she released my cock from her mouth. “Good, I want you to cum for babysitter, Sarah okay. cum in my mouth.” Sarah said before she went back to giving me a blowjob or deep throat. Deep throat is when you can feel your cock go into their throat right? I hope it is; maybe that means I’m big enough. And I’m still only 13. 🙂

“Okay… Okay… Okay…” I kept saying as my mind went blank with the bliss of her blowjob / deep throat. The problem was that all of my blood in my brain was now in my cock and I blame god because he gave us a brain and a cock and only enough blood to run one at a time. 🙂

So back to the blowjob; I was at the point of no return so I gripped onto old shoe boxes in the closet and let out a great moan or groan as I started to cum in Sarah’s mouth. I was at the stage where I could ejaculate some sperm from my cock but not as much as I’ve been told in sex-ed. I may be half-way there I think at 13.

So; I came in Sarah’s mouth and now she went into a frenzy and went faster and harder to suck out all of the cum that I could give and give me the best head of my life yet. I doubt anyone could give better but at the time, she was my first.

My orgasm must have gone on for about 10 seconds or more before it started to calm down and eventually stop. But the high from such an orgasm was mind-blowing. I couldn’t focus, hear properly and my body felt all limp.

I heard a gulp from Sarah and looked up at her to see her wipe away some of what I think was cum that had leaked out of her mouth. She looked so happy and it was because she blew me?

I steadied myself and looked at my throbbing cock, still coated with her saliva and a little of my cum and then smiled up at her. “Can we do that again?” I asked.

We laughed a little for a moment before she came in close and said. “Maybe we can do it again before you go to bed. Bed time blowjob? Would you like that Sammy?” Sarah said.

I felt myself rise to full erection right then and there and I was ready to go again and again and again. I was 13 and had an unlimited supply of orgasms for her to suck out of me. I was the luckiest 13 year old ever.

“Yes. I would like that a lot.” I said.

“What time is it anyway?” Sarah asked looking at her phone. It read 8:30 so my bed time blowjob would have to wait an hour.

I felt a little disappointed that I would have to wait an hour until my next blowjob from Sarah and she saw that look.

“Why don’t we have an early night tonight and go to bed right now?” Sarah said.

I jumped up and ran to bed in a flash and Sarah came to. That night; I think I had about five blowjob caused orgasms before I couldn’t handle it anymore and fell asleep.

In the morning; Sarah told me that I couldn’t tell anyone if I wanted to keep having her as a babysitter that would give him blowjobs. So I never told anyone except for these readers. All the names and other certain information is also changed in this story to protect myself and my babysitter.

So; after that night. I was awoken into a new world of sexual obsession and a guide to help me on my long journey.

Every time she came over; she gave me blowjobs, hand jobs, occasional titty fuck and after I turned 16 she let me have her ass for a late birthday present. My parents thought it was strange that ever though I was 16 that I still had a babysitter. They knew nothing and hopefully won’t for a very long time.

So my cousin (female) and I (male) were staying at our grandparents’ house on the same night. This has been around 3 years ago, I was 13 and she was 14. She was a mature girl even back then. Her boobs were of average size with perfectly round shape, and she had a big and shapely ass. She was naturally blonde and wore glasses, and had an hourglass figure. Some of the very first fantasies I remember having were with her. So it was getting late and we go and lay in the bed. We lay so her head is on one end and mine on the other end, and we are sort of laying at each others feet. She is wearing thin little short shorts tonight, and after laying there for a while with my hand on her thigh, I began to get very hard. I pretended I was asleep (although she very well knew I wasn’t) and began to run my hand up her leg. I worked my hand into her shorts leg and into her panties. I could feel her pussy, and she hadn’t said anything to me yet, so I started to stick my finger in and out of her. I stopped after about 5 minutes of that. When I stopped she got up and went to the other bed in the other room (I think I freaked her out a little bit, because I’m pretty sure she wasn’t entirely willing). So I layed there the rest of the night and managed to fall asleep, without finishing myself off. The next morning I woke up and went to her room. She was asleep, and I could see the edge of her bra under the tank top she was wearing. I pulled my dick out and began to jerk off to her sleeping face, and after a few minutes I took my other hand and played with one of her breasts. I had to be careful as to not wake her up. I came in the trash can next to her bed just before she woke up and made my escape. The orgasm was absolutely mind blowing.

One night when I was around 11 years old my parents were going out for the night. They hired my usual babysitter, a beautiful high school girl who was tan, tall, and had always been very dominating. Her name was Meghan and she had been my babysitter for a year. This night she made my little brother go to bed and said I could stay up with her for a while if I was good to her. I said ok and sat with her while we watched a movie. She gave me a blanket to share and we curl up next to each other under the blanket. When the movie ended she started flipping through the channels and asked what you want to watch. As she reached the porn channels she said, oh I think I know what you want to watch ha-ha. I was so embarrassed, but was even more embarrassed when she actually put one on. She asked if I was into this stuff yet and I felt her hand on my knee.

I had been just getting into sex and had only recently started masturbating but I was still confused as to what was right and wrong. I had no idea how I should feel. I was so stiff it felt like it couldn’t be moved at all and I wanted to relieve myself, but I also felt embarrassed that she would tell my parents or think I was weird for being hard or a perve for wanting it so bad.

As we watched the screen, she slowly moved her hand up my leg towards my thigh, and then slowly, she moved her hand back down my leg. Up and down up and down. Very slowly. Getting a little higher each time. As a blowjob scene came on, she asked bet you wish that was you right now. Then she giggle, and grabbed my cock, slipping her hand under my shorts. She just held it for a while, and I kept all my concentration on not cumming. I still didn’t know if it was normal to ejaculate. She didn’t say anything, just giggled every time my rock hard dick twitched uncontrollably. After a while she let go, pulled the blanket off of me revealing my boner. I tried to cover up but she said no no in a sing song voice and I let go, succumbing to my needs. She pulled my hand to the side and took my cock and put it in her mouth and began to lick and suck my cock. It felt so amazing I just gave up instantly. She did this for about 10 seconds which felt like forever before she stopped, just as I was about to cum. She said, I have always wanted to take an innocent boys innocence and then she giggled. She grabbed my dick, pulled it forward, and then let it drop with a thud on my stomach. She giggled again then started tracing circles around my head and just under the head with her finger very delicately. My cock kept twitching and I kept feeling close to orgasm, especially when shed giggle, but she would stop so often I couldn’t cum. At this point I really just wanted release even if it wasn’t right. Finally she grabbed my cock and started jerking with thumb and pointer finger very fast and I couldn’t keep it in, I came everywhere while she giggled.

When people start to talk about their childhoods, I just sit back and listen. I never tell stories about my past and what it was like for me growing up. When people ask I just say that I have a poor memory and that I can’t remember much. But the honest truth is I don’t want to remember. I have tried so hard to not remember things from my past but it doesn’t seem to work. I close my eyes and it all comes rushing back to me. At one point I told myself that I was just remembering things from a movie that it didn’t really happen to me but for some reason that hasn’t worked. I can remember everything so clearly it haunts me. I know that lay out of the room. Where the couch was, where the lazy boy chair sat, and where he was sitting when it happened. I was only 5 at the time and I am not sure why but my mom left me home alone with my sister’s boyfriend. I remember he was sitting on the chair and calling me into the living room. He asked me if I wanted to have a drink. I asked him what kind of drink and he said that it would be sweet and white like milk. All I would have to do is suck on his friend and the drink would come out. I have never told anyone this before. I have never told my mom as I know that it would kill her. I have kept it my little secret for years as I felt that no one would believe me. To this day I will not tell as I am sure it would hurt someone if I did.